Why I am approaching Heidi

I want to help Heidi scale enterprise growth.

I am approaching Heidi deliberately because I believe I can help build the enterprise sales motion for its next stage: taking a product clinicians already believe in and helping much larger health systems become confident enough to adopt it at scale.

That is a very different sale. The buying group gets larger. The questions get harder. AI enthusiasm sits beside legitimate concern about privacy, hallucination, governance, clinical risk, integration and change. My strongest contribution would be helping build a sales team that can navigate those conversations with commercial strength, empathy and judgement, while preserving the curiosity and belief that appear to make Heidi different.

The opportunity is not to bolt a traditional enterprise sales culture onto Heidi. It is to develop an enterprise capability that still feels like Heidi.
The enterprise challenge I see

Turn clinician belief into health-system confidence.

A clinician can decide Heidi makes their day better in one consultation. A health system has to decide that AI can work safely, credibly and economically across departments, systems, governance structures and thousands of people. Those are fundamentally different decisions.

Growth worth protecting

Build enterprise capability without importing the worst habits of enterprise selling.

From the outside, Heidi appears to have something valuable already: belief in the product, a strong mission and people who are excited by what they are building. Enterprise growth will need more process, qualification, forecasting and commercial discipline, but those things should support the culture rather than replace it.

I would want to help recruit and develop people who can compete hard without becoming pushy, challenge a customer without dismissing them, and help one another win rather than protecting individual territory. The strongest enterprise sellers are rarely just the loudest closers in the room.

The objective is not to make Heidi look more like a traditional enterprise software company. It is to build an enterprise sales capability that preserves the trust, curiosity and conviction that got Heidi here.
Commercial strength with empathyMove a difficult decision forward without treating scepticism as something to bulldoze through.
AI confidence without AI arroganceUnderstand why privacy, hallucination, governance and clinical-risk concerns may be rational from the customer's side of the table.
Enough product fluency to represent Heidi wellNot engineers. Sellers who understand the capability and limits well enough to lead the early conversation credibly.
Enough judgement to know what happens nextRecognise whether the issue is value, stakeholder confidence, evidence, implementation, integration or something that genuinely needs specialist depth.
The job is not to defeat the sceptic. It is to understand what they need to become confident.Know enough to lead the conversation. Know enough to recognise when you need depth. Never use the specialist as a substitute for understanding the customer's problem.
What I would build with the team

Sellers who can create confidence across a divided buying group.

Enterprise health systems will contain AI enthusiasts, cautious adopters, sceptics, blockers and people carrying very real accountability for clinical safety, data and organisational risk. The sales team needs to be able to meet all of them well, not just the people who already agree with the future.

01 · Understand

Read the person behind the objection

Is the concern about AI evidence, privacy, clinical risk, reputation, integration, change, politics or something the person is not yet saying? Treat resistance as information before treating it as an objection.

02 · Orchestrate

Build confidence across different stakeholders

A clinical champion, CIO, privacy lead, CFO and procurement team may all value Heidi differently. Help the buying organisation get to a shared decision rather than winning one stakeholder at a time.

03 · Advance

Turn belief into organisational momentum

Help the customer see enough value, evidence and credibility to introduce executive sponsors, shape a project, find budget and invest organisational energy in what comes next.

04 · Coach

Make judgement a team capability

Coach inside live deals, practise the hard conversations and make the best behaviours visible so the next seller can handle more of the complexity themselves.

That is why Enterprise Sales caught my attention.

Not because I want to arrive with a borrowed playbook and impose it. Heidi appears to be at the stage where the enterprise motion can still be shaped around what is already working. I would want to learn from the team, the customers and the deals first, then help turn those lessons into a stronger shared capability: commercially disciplined, empathetic with scepticism, confident in the product and collaborative across the wider organisation.

Healthcare is not new territory

It has been a recurring thread through my career.

Healthcare has not been the headline of my last few years, but hospitals, health departments and clinical operating environments have appeared repeatedly in my work, usually where equipment, assets, facilities, mobile work and enterprise systems meet.

From operations to enterprise technology

I understand that a hospital is an operating system before it is a software account.

My healthcare exposure started from the operational side and continued through enterprise implementations, facilities and asset systems, government health and smarter-building technologies.

That does not make me a clinician. It does mean the environment, complexity and consequences are familiar.

Australian Army · final posting
1st Field HospitalEquipment, supply, assets, purchasing, procurement and financial management in a military hospital environment.
Pinnacle · late 1990s / early 2000s
Hospital asset, maintenance, facilities and mobile systemsImplementations across organisations including St Vincent's, Royal North Shore, Calvary and St John of God hospital groups, including early mobile capability for facilities and maintenance teams.
Enterprise systems
Government health and hospital environmentsWorked with Department of Health and Human Services and other health organisations through ERP, asset management and related enterprise transformation.
IBM Smarter Buildings
Connected physical environmentsWork included concepts such as tracking mobile and high-value equipment using RFID and location infrastructure, connecting the physical environment to enterprise information.
And last week...

The thread became current again.

My wife has been a nurse for 35 years. A conversation about patient tracking, hand-offs and family communication turned into a working prototype because that is what I tend to do when somebody close to the work describes a problem.

I ask why. I try to understand the reality behind the process. Then I make a possible answer tangible enough to test.

The prototype is not my claim to healthcare credibility. The interesting part is the continuity: operational problem → curiosity → possibility → something concrete enough to discuss.
The role I am actually applying for

Help build Heidi's next enterprise sales chapter.

The Enterprise Sales leadership role is the primary conversation. I would not arrive assuming I know Heidi's sales motion better than the people already inside it. I would arrive ready to learn what is working, get into the live opportunities with the team, and help build the capability needed for increasingly complex health-system decisions across Australia and APAC.

Primary fit

Build a team that sells the outcome, not the transaction.

Enterprise Sales Leadership
The challenge I would take onFor more than a decade I have been comfortable as the first senior person in the room on new technologies and unfamiliar solution categories, or supporting that meeting through deal sponsorship. I have occupied all four seats Heidi may rely on: seller, presales, sales leader and presales leader. I understand what each person needs, where the roadblocks tend to emerge and how to coach the team through them.
Team profileInvest in people with judgement, curiosity, empathy and genuine conviction in Heidi.
Buyer orchestrationAlign champions, sceptics, executives, clinicians, IT, privacy and procurement around a decision they can support.
Deal coachingPrepare and coach the hard conversations about AI distrust, privacy, hallucination, clinical risk and change, not only the forecast.
RepeatabilityTurn what works into shared qualification, value, stakeholder and confidence habits.
The goal is not to make every seller a technical specialist. It is to give them enough product fluency, empathy and confidence to earn executive sponsorship and the next conversation, plus the judgement to know when deeper specialist support is needed.

How I would start

0-30Listen first. Get into live enterprise opportunities with the team, understand why customers buy, where confidence falls away, how current sellers work and which behaviours are already worth protecting.
31-60Coach directly in those deals. Work with the team on AI trust, discovery, qualification, value, blockers, stakeholder orchestration and executive sponsorship, while learning where the organisation can support sellers better.
61-90Begin turning the strongest patterns into a shared Heidi enterprise motion the team can learn, practise and improve, without flattening individual strengths or importing process for process's sake.

And there is an unusual extra.

When a major health-system opportunity becomes ambiguous, I am comfortable stepping into the room with the seller, helping untangle the problem, finding the language that different stakeholders can believe in and working with Heidi's specialists to shape the path forward. That is why the Deployed Product role caught my eye. Not because I want to lead with a product identity, but because it describes another place where the same customer judgement can be useful.

Why my range matters

A sales leader who can operate across the seams.

Enterprise selling at this stage will touch Bids, Product, Implementation, Customer Success and GTM operations constantly. My advantage is not that I want to own all of those functions. It is that I understand enough of each world to connect them around the customer and help the sales team use the organisation well.

My primary job

Build enterprise sales capability.

Discovery, value, qualification, stakeholder strategy, executive sponsorship, deal coaching and a repeatable way of turning customer interest into confident organisational decisions.

The seamCustomer reality
→ judgement
→ capability
The uncommon extra

Go deeper when the situation demands it.

I can work credibly with operational users, product and technical teams when a major customer problem needs more than a standard answer, without turning every sales conversation into a technical exercise.

Sales leadership

Coach the judgement

Make discovery, value, stakeholder strategy and decision risk visible early enough to change the outcome.

Evidence: Decision Confidence + Symphony
Bids

Keep the story coherent

Connect what Sales learned about value and stakeholders to the formal procurement response instead of treating the tender as a separate event.

Evidence: Tender Response work
GTM systems

Remove avoidable friction

Use automation and AI where they improve preparation, follow-through and visibility, without confusing tooling with selling.

Evidence: GNR8 / Harper
Product + implementation

Bring the right people in well

Know when the opportunity needs deeper workflow, product or implementation expertise and give those specialists a well-framed problem to solve.

Evidence: 25+ years across the seam
My technical fluency matters because it lets me have the conversation. My value is knowing what conversation needs to happen, and helping the team become better at having it.
Proof, not positioning

The pattern existed long before I had language for it.

A few examples matter more here than a complete career history. Each one says something about how I behave when the playbook is incomplete.

TechnologyOne

Treat the constraint as evidence

A critical maintenance transaction took 48 seconds in the customer's old system and about five minutes in the replacement. I did not defend the product. I treated 48 seconds as the design constraint and helped reshape the workflow around the actual task.

PowerPlan

Build the market, not just the pipeline

Joined as employee number one in APAC, built the regional operation, partners and pipeline, and secured a 10-year Victorian Government agreement with TCV above A$13m.

Enterprise leadership

Coach where the deal is happening

Led solution and presales teams at IFS and BlackLine, with 160% FY21 at IFS and 10 of 12 quarters above target at BlackLine. The useful part was always getting into the difficult deal, not watching it from a dashboard.

GraysOnline

Create confidence before demanding behaviour change

Helped move high-value industrial assets online when the market believed serious buyers would not purchase that way. Better information, inspection evidence and trust changed the behaviour.

Pinnacle + field work

Design with the operator, not for them

Worked across consulting, professional services and mobile-work design, translating maintenance, procurement and field processes into something useful away from the desk.

Applied AI now

Make ideas testable

Built multi-tenant AI products spanning deal intelligence, research, roleplay, retrieval, marketing automation, outbound action, job intelligence and assurance. I am not a conventional developer. I am a solution person who can now build enough to prove the answer.

Why the things I build matter

The things I have built are evidence, not the headline.

I build when I see a recurring problem that should not depend on one exceptional person remembering what to do. Each product below turns observed friction into a repeatable way for other people to make better decisions and execute with more confidence.

Symphony

Make complex enterprise selling coachable.

Built around the recurring failure of deals being managed by stage while qualification, stakeholder dynamics and decision risk stay hidden. Symphony brings together enterprise qualification, buyer orchestration, Decision Confidence, live deal coaching and roleplay practice so judgement can be developed and repeated across a team.

Tender Response

Keep formal responses grounded and reusable.

Built to stop tender and RFP work becoming a fresh scramble of copied claims. It uses reusable knowledge, grounded response drafting and validation so teams can answer consistently, show their evidence and improve the knowledge base after each submission.

GNR8 / Harper

Turn GTM intent into controlled execution.

Built to address the gap between a commercial plan and the many research, preparation, follow-up and approval steps needed to carry it out. Agentic workflows coordinate the work while keeping human judgement and control where they matter.

Phoenix

Support a difficult human decision with applied AI.

Built around the complexity of matching people to opportunities when a title or keyword search is not enough. It turns fragmented job and candidate signals into structured decision support that helps a person judge fit with better context.

The useful signal for Heidi is not technical depth for its own sake. It is agency: I notice a persistent business problem, work out the judgement that matters, make an answer tangible and turn it into capability other people can use.

Symphony, GNR8, Phoenix and the tender-response work belong this far down the page deliberately. They show range, agency and the ability to make ideas concrete. They are not the proposition. The enterprise sales motion is.
Your filter questions

I noticed what Heidi is really screening for.

The application form is conventional. The filter questions are not. They are testing agency, appetite for ambiguity, willingness to build, and whether somebody actually wants to get into the problem.

Can you execute without a legion of support?
Yes. That is probably the easiest one.

For more than a decade I have been the first senior person in the room, or the deal sponsor behind that person, when the technology or solution category was new. I have done it as a seller, presales professional, sales leader and presales leader. I can lead the early conversation, give the team confidence, anticipate the roadblocks and help earn the next meeting without pretending to hold every technical answer.

Have you shipped something this week?
Yes. A healthcare workflow prototype was part of it.

The recent patient-tracking and family-communication prototype is exactly the sort of small, concrete experiment I use to understand whether an idea deserves to become something bigger.

Have you brought difficult deals back to life?
Yes, but pressure is rarely the answer.

My instinct is to work out why the buying organisation cannot move, whose confidence is missing, what value is unproven, or which assumption is wrong. That thinking eventually became Decision Confidence and Symphony.

Does making health systems better matter?
Yes, and the connection is older than this application.

Healthcare has appeared throughout my career from 1st Field Hospital through hospital asset, facilities, mobile and enterprise systems. Living with a nurse for decades also gives the operational frustrations a very human context.

Are you good at games? Did you have a weird teenage hobby?
I will leave Heidi at least two questions to ask me in person.

The work questions are easy to evidence. The weird ones are probably better conversation than application-form content anyway.

Where I would start

The Enterprise Sales role is the reason I am here. The broader capability is why I may be unusually useful.

I am most interested in helping Heidi build the enterprise sales capability for the next stage of growth: strong enough commercially to win difficult health-system decisions, empathetic enough to understand the people who are not yet comfortable with AI, and collaborative enough to preserve the kind of team culture that appears to make Heidi special.

If that is the challenge behind the role, I think we should talk. And if somewhere along the way Heidi also needs a senior person who can step into one of the strange, high-value customer problems that does not fit neatly inside a box, that is a useful extra.

rick@teamsolutionsgroup.com.auLinkedIn
The proposition in one sentence

I am not trying to squeeze myself into every vacancy at Heidi. I am interested in the enterprise sales leadership challenge. The other roles simply made something clearer: the strongest version of that sales organisation will connect commercial discipline with empathy, AI fluency, buyer orchestration and genuine curiosity about the customer's problem, without losing the culture that made people believe in Heidi in the first place.

Role context reviewed September 2026: Enterprise Sales Manager · Deployed Product Manager · Bid Manager